Both are c. 1940s made by Superior. Features comic strip characters from Chicago Tribune Syndicate including Orphan Annie, Dick Tracy, Smitty, and Winnie Winkle. First set is #404. Box is 3-7/8x7.25x7/8" deep with three panel comic strip on lid. Contains 2x6" pad with comic strip on top and blank pages to use with ink stamps. Comes with five character stamps including Orphan Annie with Sandy, Dick Tracy, B.O. Plenty, Denny Dimwit, and Smitty talking to Herby. Each stamp is 1" tall. Box has trace of lt. edge wear and some lt. dust soil. Fine. Stamps show some use and are VG/Fine. Second set is #4085 and is 9.75x11x.75" deep with five panel comic strip on lid top with different scenes than smaller set. The same characters are shown along with Junior, Punjab, Mr. Bailey, and Perry Winkle. Die-cut insert holds 14 ink stamps ranging in size from 3/8x7/8" to 1x2.25". Comes with 3x8.75" paper tablet with cover paper with three panel comic strip which is a bit similar to smaller set but has different dialog and also includes instruction folder. Set also includes larger ink pad and boxed crayons. Box lid has color rubs around edges and is missing .25" bit of surface paper at center of bottom panel. Fine/VF. Contents are VF+ and show little use. Both are nicely designed with wonderful art.